People Operations Generalist

Salary: $75-80k annually

Benefits: Free employee-only medical coverage under one of our plans. Free short-term disability and FREE life insurance coverage.  Plus, a 4% employer match with our 401(k).  Other incredible benefits HERE.

Location: Candidates in Chicago, Houston, Austin, or Phoenix will be considered

Your Mission:

Your mission is to ensure the seamless execution of Playbook’s core people operations by managing talent acquisition, payroll administration, and benefits compliance with precision and care. As one part of a two-person People Operations team, you’ll get the opportunity to work within every facet of HR. You’ll serve as the connective force between candidates and Playbook, driving efficiency, clarity, and consistency across every stage of the candidate experience. 

The Legacy You'll Leave:

You supported the evolution of a streamlined, high-performing People function that balanced precision with empathy. Through your consistency and attention to detail, you elevated the candidate experience and strengthened trust across teams. Your impact was felt in every hire made, every process improved, and every employee who felt supported through precise, efficient, and people-centered operations.

• Lead full-cycle talent acquisition. Guide candidates through every stage of the hiring process with care and professionalism, ensuring each new hire reflects our values, strengthens our culture, and supports the company’s growth.
• Own the candidate pipeline. Keep candidate pipelines organized and moving smoothly, maintaining accuracy and communication so every applicant feels valued and informed throughout their journey.
• Champion the candidate experience. Create a thoughtful and engaging experience for every candidate while partnering closely with Hiring Managers, our Executive Assistant, and our Senior Director of People Operations to build strong, connected teams.
• Drive continuous improvement. Use insights and feedback to refine recruiting processes, enhance sourcing strategies, and continually improve the way we attract and welcome top talent into our company.
• Oversee benefits compliance. Partner closely with our insurance broker, Sequoia, to maintain ongoing healthcare compliance, complete quarterly tasks, and keep the Sequoia People Platform up to date. Stay ahead of deadlines by reviewing compliance checklists regularly and collaborating with the account manager for guidance and clarity.
• Administer and prepare payroll. Coordinate biweekly payroll activities for contractors and host teams, ensuring job codes, time approvals, and contractor communications are accurate and complete. Maintain clean, organized systems so every team member is paid correctly and on time.

• You have at least 3 years of experience as an HR Generalist or HR Coordinator.
• You have a minimum of 2 years of experience managing the full talent acquisition life cycle, including sourcing candidates, ideally within the hospitality sector.
• Experience managing an Applicant Tracking System (Lever experience is a plus).
• Exposure to or experience with HR compliance processes and requirements.
• You have experience operating an HRIS (Rippling experience is a plus).

• You sweat the small stuff. Accuracy matters to you; from recruiting to payroll to compliance, you keep data clean, details sharp, and documentation flawless.
• You’re a clear and caring communicator. You build trust at every touchpoint, with candidates, employees, leaders, and partners; through empathy, honesty, and follow-through.
• You show up ready to “Pick Up an Oar.” Collaboration is your default mode. You partner seamlessly with Hiring Managers, the EA, the Senior Director of People Operations, and external partners to row in the same direction and reach shared goals.
• You keep chaos in check. You’re organized, proactive, and excellent at juggling priorities, maintaining pipelines, payroll, compliance, and systems without missing a beat.
• You embrace change with curiosity. You seek better ways to do things, use data and feedback to spot opportunities, and make HR processes more efficient, consistent, and human.

Our Core Values:

Playbook's culture is based on a shared respect for our lived values HERE.  Fit with our values is a critical component of our hiring process, and you and all of our colleagues are expected to live our core values in interactions with team members, customers, and stakeholders.  An assessment of how you have exhibited our values is also an important part of your performance review process.

Our Commitment To You:

Playbook is committed to building a team that represents a variety of backgrounds, perspectives, and skills.  We know the more inclusive we are, the greater our impact will be!

A Quick Note About Salaries:

We list salaries based on a few key factors.  These include location-specific budgets, market trends, team size, and the scope of the building.  Since we’re a national company working with office properties of all shapes and sizes, the listed salary is tailored specifically to this role and may differ from similar-titled roles on our Careers Page. Curious or want to chat more about it?  We promise to be open and transparent about these details throughout our interview process.